The 90-Day Autonomy Roadmap

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Turn All Of This Into A 90 Day Autonomy Plan

Over the last seven weeks you have gathered a lot of pieces like a clear definition of what an autonomous business means for you, a list of your main flows, at least one simple playbook, decision rules for common choices, a basic ownership map, a light weekly rhythm and a way to decide what stays human and what can be AI supported.

This week is about turning all of that into a simple, practical 90 day plan.

Not a grand transformation. Just three focused months where your business becomes meaningfully less dependent on you.

The problem in plain language

Without a plan, everything you have built so far is at risk of fading into the background. You know this pattern, you learn helpful ideas, you make some changes and then the week fills up.

A few busy months go by, and you are back to answering the same questions, stepping into the same flows, telling yourself that you will “fix the system” when things calm down

On top of this, AI options are everywhere. You hear that you should be using assistants, automation, and all kinds of tools. That can create a quiet pressure to do something big and clever, which often leads to no action at all.

A 90 day plan gives you a different path. It is short enough to feel real, long enough to make real changes and lets you choose a few things and ignore the rest for now

The rest of this issue will help you build that plan in a calm, steady way.

A tactical framework: three 30 day phases

You can think of the next 90 days in three stages.
→Stabilize and see clearly
→Strengthen rules and ownership
→Add small AI support in safe places

Your goal is not to “finish” autonomy. It is to walk through these three passes on a small set of flows so you feel the difference in daily life.

Days 1 to 30: Stabilize and see clearly

In the first month, you keep things simple. You focus on clarity and consistency.

1. Choose two or three core flows

   →For example: new lead handling, new customer onboarding, support requests
   

2. Make sure each has a basic playbook
   →For each chosen flow, you want: Name, Trigger, Outcome, Steps, Roles and owners, A few notes
   

3. Confirm the owner for each flow
   →The owner is not you, if that is at all possible. If it must be you for now, write that on purpose rather than by default.
   

4. Run the weekly check in
   →Use your simple rhythm from last week to see how these flows behave.

Ask what worked, what did not, and what small change to try. This is mostly “traditional” work. People follow playbooks and you watch what happens. AI is in the background for now.

Days 31 to 60: Strengthen rules and ownership

In the second month, you add more structure and push ownership further away from you.

1. Add decision rules to each chosen flow
   →Look at where people still hesitate or ask you.
   →Create three to five short rules for those points.
   

2. Adjust rules based on real use
   →Each week, owners bring back where rules helped and where they did not.
   →You tweak wording, thresholds, or who escalates what.
   

3. Clarify how you want to be involved. For each flow, write one short note:
   
   →When you want to be informed
   →When you want a say
   →When you do not need to see the details
   

4. Continue the weekly rhythm
   →Owners share what they saw. You keep the changes small but steady.

By the end of day 60, your chosen flows should feel more predictable. People know what to do most of the time. You are still involved, but less as a firefighter and more as a guide.

Days 61 to 90: Add AI support in safe spots

In the third month, you add AI support where it makes sense. You already have the tools you need to choose where:

→Your volume and risk view from last week
→Your labels for “human only”, “AI supported”, and “AI first candidate”

1. For each chosen flow, pick one “AI supported” step. For example:
   →Drafting first replies for basic support questions
   →Drafting follow up emails after sales calls
   →Summarizing notes before a client review
   

2. Write a very clear rule for that step. Include:
   →What input the AI sees
   →What it should produce
   →Which rule or template it should follow
   →Who reviews and sends or approves
   

3. Test in a small, contained way. Start with:
   →AI drafts, human sends
   →AI tags, human checks and adjusts
   

4. Use the weekly check in to review. Owners bring:
   →What the AI did well

   →Where it made things easier
   →Any mistakes or friction

You only need one or two good AI supported steps per flow to feel a difference. You are not trying to automate everything. You are removing a layer of repetitive work from your plate and from your team.

A simple example: a 90 day path for a small SaaS

Imagine a founder named Maya who runs a small SaaS product with a team of three. She chooses three flows:

→New trial signups
→New customer onboarding
→Support requests

Days 1 to 30

She writes short playbooks for each flow.
→For new trials: how they are welcomed, when they receive help, when they are invited to book a call.
→For onboarding: what happens from first payment to “fully set up”.
→For support: how tickets are received, answered, and closed.

She confirms owners.
→Sales and trials: Maya, for now.
→Onboarding: customer success person.
→Support: support lead.

She starts a 30 minute weekly check in to review these three areas.

Days 31 to 60

They add decision rules.
→For trials: when to offer a call and when to let people explore alone.
→For onboarding: when to schedule an extra check in.
→For support: when to refund, when to offer credit, when to escalate.

The owners bring notes each week. They adjust rules that did not match reality.

Maya also writes one short note for each flow about how she wants to be involved. For example, she decides she only wants to be pulled into support when there is a likely churn risk or a serious bug.

Days 61 to 90

They add AI support to a few safe spots.
→Support: AI suggests categories and draft replies for basic questions. Support lead reviews and sends.
→Trials: AI drafts a follow up email for people who signed up seven days ago but have barely used the product. Maya checks the first few, then lets the system run with oversight.
→Onboarding: AI generates a short summary of each new customer’s context based on their answers and sends it to the success person before the kickoff call.

Every week, they look at how these changes behaved.
→Did support get faster without losing quality
→Did follow ups feel personal and on brand
→Did the summaries save time preparing for calls

At the end of 90 days, the business is not perfect. It is different though.
→The core flows are clear and written
→Rules handle many small decisions
→Owners know what is theirs
→A simple rhythm keeps things improving
→AI support takes some first passes, always under a person’s eye

Maya still has work on her hands, but she is no longer the default answer to every question. The business has started to stand on its own legs.

Tip of the week

Sketch your 90 day plan on a single page. Create three sections- Days 1 to 30, 31 to 60 and 61 to 90.

Under each, write three short lines:
→Flows we focus on
→Systems changes
→AI support experiments

For example: Days 1 to 30

→Flows: trials, onboarding, support
→Systems: write playbooks, confirm owners, start weekly check in
→AI: none yet, just observe

You should be able to read this page in under a minute and know what you are doing each month.

If it feels crowded, remove items until you are down to what you can realistically move in normal weeks, not ideal weeks.

One clear next step before next week

Before you close this week’s issue, choose one of these actions and do it today:

→Block a 45 minute slot on your calendar to finish your 90 day page and share it with your team
→Email your team with the three flows you want to focus on and ask who is willing to own which
→Pick one “AI supported” step and write a three line description of how you want it to work

You now have everything you need to make real progress in the next three months. The rest is small, steady steps: flows, rules, ownership, rhythm, and a few carefully chosen places where tools and AI handle the routine work so you can focus on the parts that still need you most.